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  • Ryan and Skylar

December Dates #4


That's 7 dates in 7 days. A modern-day Snow White and the Seven Dwarfs perhaps?

Key Takeaway: I am not ready to date. At all. Even a little. And overdoing it made it even more obvious.

Why did I do this? I could not explain. It was rough. It was fun. It was a dumb goal I made.


Dopey loves his own opinions. We took a walk to a coffee shop and spent about an hour together. He was REALLY cute to look at, but talking to him was like hearing a college professor in a 101 class explain basic English and film theory. This was frustrating mostly because sometimes his “facts” were objectively untrue. But the confidence on this man! It was seriously impressive. When it came time to say goodbye, I figured maybe he was just nervous or trying to fill the silence. I texted him once after and never got a reply.


Grumpy hated me. Outright. It was clear because he did not try to hide it. He was wealthier than I was, pursuing a career in banking, and did not have the remotest respect for my aspirations in standup and writing. He was bourgeois, young, and mentioned five brand names in a row (something I care nothing about). He literally rolled his eyes when I talked about how I was happy to be making ends meet, which ended it for me. Respect is the bare minimum you can give. So I left 30 minutes into our walk around the park.


I named him Sleepy because I was the sleepy one. We kept having to push back the hangout. Back and back and back and back. By the time we met in his backyard, it was around 11pm and I’d worked and done an open mic already. He also decided to tell me all about how I should be structuring my jokes. This bothered me. A lot. And he went on and on and on and on and on until I... fell asleep. Sometime after 1am I had fallen asleep. He was very offended. I don’t blame him. But also I do blame him for correcting me having never seen me perform. Anywho, he was Australian and that was cool.


Happy was a sweet guy! We took a walk around my neighborhood in Christmas sweaters and stopped for a coffee. We were getting along, clicking like we’d known each other for a while. Then, he informed me that he was married. That’s right. It happened twice during this December experiment! Please tell people when you’re married! Please! It’s tough to navigate when you start to enjoy somebody.


I left the date with Bashful early. It turned out I was his first “date” with a guy. We walked around a park and I tried to carry the conversation, but he kept looking around like we were being followed instead of talking to me. When I asked, he explained that he hadn’t told anybody he was exploring being gay. Personally, I don’t like being someone’s experiment. It’s hard to get to know someone when they’re fully panicked. I left after 30 minutes of trying to get him to relax.


I was trying to remember if anyone sneezed this week. And one guy did! So he gets to be Sneezy. I like Sneezy on paper. He travels, he has a creative career, he has ambition. There was just something missing. We grabbed some pizza and took a walk outside, but ultimately there isn’t much to report here. There just was no chemistry and it was clear he thought I was attractive where I didn’t necessarily feel the same way in person. I felt bad about this as he was objectively good to look at. I just was not feeling it and I’m learning to be okay with that.


Doc was... older than advertised. He was sweet, he was fun to talk to, but he was more than twice my age. He didn’t look it! But when I asked, despite my belief that age is just a number, I realized that age is also an expression of experience. We chatted for about two hours outside of his house, enjoying getting to know each other. But I couldn’t really feel anything romantically for him. When he went in for a kiss as I left, I said “no thank you.” Then I apologized profusely, not wanting to be rude.

So what have I learned here?

I’m not ready to be dating people. I like myself, I like time by myself, and I need a few months (at least) alone to get things done. It’s not that I’m closed off to the right person, but the energy I put into swiping and chatting could be better utilized elsewhere. Like sitting quietly in a room and listening to music. Or doing literally anything else.

It’s hard because I really care for Kevin (one of the people I’ve met up with), but I am not happy when I’m exploring romance right now. And I hope he is okay with just being my friend for a good while.

And I had something with a lot of good with my ex. I left because I wanted to give myself the time to learn who I am alone. He’s a tough comparison to make as I spent a lot of time knowing him. I need to just be okay with being in a room without anyone else there.


Key Takeaways: The cell service in the middle of nowhere is nonexistent (this is something I hope my date took away)


Name: Rocky because he's into rock climbing and I don't feel particularly creative at the moment

Length of date: 25 minutes

How the date was obtained: Bumble

Where: The comfort of my own home, once again.

A couple weeks ago I discovered the conveniences of FaceTime dates and ever since, I've been hoping to set up more of them. They take minimal effort, which makes them ideal for first dates that you don't want to invest a lot into yet. I was looking forward to only focusing on getting to know Rocky, who seemed like a super interesting guy. He frequents a rock climbing/bouldering gym, he got scuba certified this past year, and he loves to snowboard. I don't do any of those things, but how fun would it be to learn!

Before our virtual date, I moved a couple of things out of my background (Rocky didn't need to know that I'm messy yet) and made the call out to him. Somehow, despite having confirmed the time earlier that day, my first impression was that I had caught Rocky very, very off guard. He was in the car driving, the phone was mounted on his dashboard, and he asked me to wait a second so he could "get me over the car Bluetooth."

Maybe he was almost home and hadn't wanted to ask for an extra 10 minutes before the call? Weird, but okay. Come to find out, he was coming back from off-roading in the desert and was TWO HOURS out.

Maybe he wanted someone to talk to on his long road trip? Car rides can be lonely so I understand that. I had already planned on spending a couple of hours talking to him, so I guess it didn't matter where he was that much. Really all you need is cell service.

Except he didn't have that. Somewhere between the three disconnected calls we had, he mentioned that "he always has this problem when he's coming back from the sand dunes." I guess he had not learned from those past experiences, or this date wasn't particularly important to him.

I did not have the time or energy to continue playing phone tag with Rocky and was starting to get irritated with his lack of planning. The great thing about FaceTime dates is that they take minimum effort. Literally the ONLY thing you have to do is show up and be somewhere that you're able to talk. No driving, no intense getting ready process, no choosing a place to meet. And pretty much everywhere has cell service (except the place Rocky chose to call me from). After another dropped call, I sent him a message saying the cell service was clearly not good for him and there was no point in continuing to FaceTime right now when we would get interrupted every 5 minutes.

It was unfortunate because I had gone into the date with only good feelings about Rocky and from the maybe 15 minutes of conversation we actually had, he was just as funny and interesting as I expected. I suspect that Rocky is a genuinely decent guy with the planning skills and forethought of a child.

Overall Experience:


The future for us… It's tough to say because I don't feel like I got a chance to get to know Rocky more at all. The circumstances were not ideal, but he did choose those circumstances. Overall, I felt like the date was an afterthought and he didn't care enough to try to re-plan. I don't feel particularly inclined to talk to him anymore, but might be receptive if he reached out to try again. I don't think a second date would do any harm.

Next Week: This was my last blog post, so there's no date next week! This was lot of fun and definitely made me feel less dating pressure. That's a success in my book!


Hey! It's me, Isabel.

I want to say a huge "THANK YOU" to Skylar and Ryan for their amazing blog posts! I know them both personally, and anyone would be lucky to spend time with them! I wish them nothing but the best.

Also, if you haven't already, go check out my post on It was Date #52, the final date of my Date a Week LA journey! Read about my final date, what I learned, and how immensely grateful I am.


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